#------------------------------------------------------------------------------ #$Date: 2008-01-26 13:05:32 +0000 (Sat, 26 Jan 2008) $ #$Revision: 19 $ #$URL: svn://www.crystallography.net/cod/cif/2/2011927.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_2011927 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2001 _journal_volume 57 _journal_page_first 593 _journal_page_last 596 _publ_section_title ; Novel heterocyclic inhibitors of matrix metalloproteinases: three 6H-1,3,4-thiadiazines ; loop_ _publ_author_name 'Schr\"oder, J\"org' 'Wenzel, Herbert' 'Stammler, Hans-Georg' 'Stammler, Anja' 'Neumann, Beate' 'Tschesche, Harald' _chemical_formula_moiety 'C18 H17 F N4 O3 S2' _chemical_formula_sum 'C18 H17 F N4 O3 S2' _chemical_formula_weight 420.48 _symmetry_cell_setting 'orthorhombic' _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.675(19) _cell_length_b 12.704(19) _cell_length_c 15.606(15) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1918(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _exptl_crystal_density_diffrn 1.456 _diffrn_ambient_temperature 173(2) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol S1 .09325(6) .77278(5) .31052(4) .02420(14) Uani d . 1 . . S S2 .17513(7) .50883(5) .58954(4) .02467(14) Uani d . 1 . . S N1 .3671(2) .8371(2) .22849(14) .0289(5) Uani d . 1 . . N N2 .3699(2) .8075(2) .31511(14) .0285(5) Uani d . 1 . . N N3 .2754(2) .76999(19) .44485(13) .0224(4) Uani d . 1 . . N H3N .363(4) .759(3) .463(2) .037(9) Uiso d . 1 . . H N4 .1390(2) .62762(18) .62024(13) .0232(4) Uani d . 1 . . N H4N .052(5) .634(3) .637(3) .051(12) Uiso d . 1 . . H O1 .04966(18) .77390(17) .48789(12) .0279(4) Uani d . 1 . . O O2 .3221(2) .49252(17) .60224(12) .0350(5) Uani d . 1 . . O O3 .0773(3) .44185(17) .63244(13) .0352(5) Uani d . 1 . . O F1 .3034(3) .9218(2) -.16711(12) .0593(7) Uani d . 1 . . F C1 .2067(4) .7757(2) .02291(18) .0349(6) Uani d . 1 . . C H1 .1514 .7170 .0386 .042 Uiso calc R 1 . . H C2 .2143(4) .8060(3) -.06292(19) .0425(8) Uani d . 1 . . C H2 .1649 .7688 -.1059 .051 Uiso calc R 1 . . H C3 .2953(4) .8915(3) -.08354(18) .0375(7) Uani d . 1 . . C C4 .3687(3) .9493(3) -.02380(18) .0335(6) Uani d . 1 . . C H4 .4228 1.0083 -.0404 .040 Uiso calc R 1 . . H C5 .3604(3) .9181(2) .06178(17) .0285(5) Uani d . 1 . . C H5 .4100 .9562 .1042 .034 Uiso calc R 1 . . H C6 .2797(3) .8307(2) .08625(16) .0238(5) Uani d . 1 . . C C7 .2741(3) .7991(2) .17787(16) .0228(5) Uani d . 1 . . C C8 .1631(3) .7255(2) .20965(16) .0298(5) Uani d . 1 . . C H8A .2024 .6542 .2177 .036 Uiso calc R 1 . . H H8B .0882 .7207 .1666 .036 Uiso calc R 1 . . H C9 .2571(3) .7875(2) .35682(15) .0212(4) Uani d . 1 . . C C10 .1728(3) .75567(19) .50393(15) .0214(4) Uani d . 1 . . C C11 .2220(3) .7174(2) .59211(15) .0236(5) Uani d . 1 . . C H11 .3211 .6956 .5881 .028 Uiso calc R 1 . . H C12 .2083(4) .8058(3) .6576(2) .0392(7) Uani d . 1 . . C H12A .1109 .8259 .6630 .059 Uiso calc R 1 . . H H12B .2624 .8668 .6387 .059 Uiso calc R 1 . . H H12C .2428 .7816 .7133 .059 Uiso calc R 1 . . H C13 .1483(3) .4990(2) .47732(15) .0238(5) Uani d . 1 . . C C14 .0141(3) .4948(2) .44451(17) .0278(5) Uani d . 1 . . C H14 -.0637 .5002 .4814 .033 Uiso calc R 1 . . H C15 -.0030(3) .4825(2) .35636(18) .0316(6) Uani d . 1 . . C H15 -.0935 .4809 .3327 .038 Uiso calc R 1 . . H C16 .1113(3) .4726(2) .30260(17) .0324(6) Uani d . 1 . . C H16 .0983 .4627 .2428 .039 Uiso calc R 1 . . H C17 .2444(4) .4770(3) .33623(19) .0391(7) Uani d . 1 . . C H17 .3221 .4703 .2994 .047 Uiso calc R 1 . . H C18 .2639(3) .4913(3) .42403(17) .0361(6) Uani d . 1 . . C H18 .3545 .4958 .4473 .043 Uiso calc R 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S1 .0176(2) .0352(3) .0198(3) -.0027(2) -.0020(2) .0014(2) S2 .0276(3) .0302(3) .0162(2) .0046(3) -.0007(2) .0030(2) N1 .0253(10) .0446(13) .0170(9) -.0067(10) -.0006(8) .0072(9) N2 .0205(9) .0471(13) .0180(9) -.0046(9) -.0028(8) .0079(9) N3 .0173(8) .0325(11) .0173(9) -.0011(9) -.0008(7) .0037(8) N4 .0205(9) .0310(10) .0181(9) -.0007(9) .0041(8) .0019(8) O1 .0172(7) .0428(11) .0237(8) .0023(8) .0002(6) .0060(8) O2 .0312(9) .0472(11) .0266(9) .0166(10) -.0058(8) -.0006(9) O3 .0473(12) .0334(10) .0248(9) -.0064(10) .0043(9) .0066(8) F1 .0914(18) .0667(14) .0197(9) -.0189(14) .0008(10) .0077(9) C1 .0509(18) .0305(13) .0233(12) -.0073(13) -.0033(11) .0011(11) C2 .067(2) .0407(16) .0201(12) -.0077(16) -.0079(13) -.0029(11) C3 .0500(19) .0445(16) .0179(12) .0002(14) .0022(12) .0061(11) C4 .0329(13) .0420(15) .0257(13) -.0041(13) .0043(11) .0071(11) C5 .0239(12) .0387(14) .0228(11) -.0048(11) .0013(10) .0032(10) C6 .0250(11) .0284(11) .0181(10) .0015(10) .0017(9) .0012(9) C7 .0237(11) .0262(11) .0185(10) .0016(9) -.0001(8) .0013(8) C8 .0371(14) .0320(12) .0202(11) -.0104(12) .0012(10) -.0028(10) C9 .0217(10) .0250(11) .0169(10) -.0002(9) -.0013(8) .0026(8) C10 .0201(10) .0278(11) .0162(9) -.0015(9) .0001(8) .0017(8) C11 .0205(10) .0339(12) .0165(9) -.0041(10) -.0014(8) .0033(10) C12 .0525(19) .0383(15) .0267(13) -.0128(14) -.0015(13) -.0076(12) C13 .0275(12) .0265(11) .0176(10) .0006(10) -.0011(8) .0007(9) C14 .0271(12) .0338(14) .0225(11) -.0012(11) .0012(9) -.0021(10) C15 .0360(14) .0348(14) .0241(12) -.0094(12) -.0061(10) -.0011(11) C16 .0467(16) .0328(13) .0177(11) -.0083(12) .0003(11) -.0011(10) C17 .0418(16) .0525(19) .0229(12) -.0022(15) .0084(11) -.0041(12) C18 .0290(13) .0563(19) .0230(13) .0036(14) .0017(10) .0010(13) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S1 C9 . 1.752(4) y S1 C8 . 1.816(3) y S2 O3 . 1.438(3) ? S2 O2 . 1.451(3) ? S2 N4 . 1.621(3) ? S2 C13 . 1.775(3) ? N1 C7 . 1.291(4) y N1 N2 . 1.404(3) y N2 C9 . 1.296(4) y N3 C10 . 1.367(3) ? N3 C9 . 1.403(3) y N3 H3N . .90(4) ? N4 C11 . 1.463(4) ? N4 H4N . .88(5) ? O1 C10 . 1.239(4) ? F1 C3 . 1.362(3) ? C1 C2 . 1.396(4) ? C1 C6 . 1.401(4) ? C1 H1 . .9500 ? C2 C3 . 1.377(5) ? C2 H2 . .9500 ? C3 C4 . 1.383(4) ? C4 C5 . 1.396(4) ? C4 H4 . .9500 ? C5 C6 . 1.410(4) ? C5 H5 . .9500 ? C6 C7 . 1.486(4) ? C7 C8 . 1.508(4) ? C8 H8A . .9900 ? C8 H8B . .9900 ? C10 C11 . 1.535(4) ? C11 C12 . 1.524(4) ? C11 H11 . 1.0000 ? C12 H12A . .9800 ? C12 H12B . .9800 ? C12 H12C . .9800 ? C13 C14 . 1.397(4) ? C13 C18 . 1.397(4) ? C14 C15 . 1.394(4) ? C14 H14 . .9500 ? C15 C16 . 1.394(5) ? C15 H15 . .9500 ? C16 C17 . 1.392(5) ? C16 H16 . .9500 ? C17 C18 . 1.395(4) ? C17 H17 . .9500 ? C18 H18 . .9500 ?